Phosphatidic composition



No'Drawing.

. i 1 v A u; 7.* I I 211.41.71 t y l rnosrna'riprc reclaim. (cl. zeef-4oz) lhis invention relatesI to phosphatidic compositions, and more' particularly to compositions of matter produced' by phosphatides salts ofhydroxy'acids. f o

In accordance lwith the present` invention, has been found that pl'icisphatidees` and salts of hydroxy acids form compositions which vhave important new properti have a hydroxy acid cal, which may comprise an alkali metal, an alkali earthy metal, ammonia ble 'ofreacting with organic acids to form salts. By hydroxy acid is meant an organic compound having an acid reaction hydroxy group. Phosphatides and. itis believed y are` amphoteric or an amine capathat'the hydroxy group of the` The salts referred vto radical and an alkaline radi-4A` vl and at least one free acid radical enables the: sans to ycombine with the phosphatide radical fof the' phosphatides', but the chemistry is vextremely.complex, and applicantfdoes not wish to beboundl by any precise theory. The nature ofthe resultant product indicates that true'y chemical compounds are formed. That'isfto say, the' resultant products exhibit physical and chemical evidence of being actual chemical compounds by every employed. Of `the' broa tions referred to. Athose which appear to have the vgreatest utility yatthe present time result from treating phosphatides kwith alkali metal or ammonium salts cf water' acids. In

test I have l soluble edible hydroxy. addition to other desirable properties.

class'of .compounds or composi(` such compoundsjare suitable for incorporation into fojod products as water retention agents and for increasing tliesuga'rv tolerance of baked proditv is preferred to emr-1 ucts.'l `For s ch purposes ploy vegetable phosphatides vwhich are free of linolenic yacid radicals. the' preferred phosphatide being corngphosphatide and the preferred sc .ltV

being sodium lactate.

It is;` therefore`,-an "object lof the present in? vention to provide a new tion with salts ofhydroxy acids.

Another ol'rlect` ofthe' inv ntion is to provide i a new composition of matter resulting from treat-i ing vegetable phospha'tides4 with edible water soluble hydroxy acids.

Another,objectfof thel invention is to provide 4a new composition of matter resulting from treatf ing vegetable phosphatidesI free ofj linolenic acid radicals with ammonium or alkalikmetal saltsjof edible waterQsoluble hydroxy acids.' Y n Another vobject of the inventionisto provide an improved pableof being incorpor ted into foodvproducts to edible phosphatidic composition ca n employed, the "gre ter increase water retention or the sugar tolerance of baked products. w v y .l

Another object of the invention is toprovide an improved phosphatidic composition resulting from treating 1icgetable phosphatides with alkali tions,

metal sans or edible wer' solublecayeron'una.A

which Icomposition"'truly' be combined 'with short l Keningor to high sugarratio .e and non-spatteringtype: yAnother object-ot the invention isto provide a process ofl producing phosphatidicfcompositions in which phosphatides are treated witlrsalts of A1 stillf'urther' object of theinvention is toprovide a process ofproducingnewphosphatidic V compositions` of vegetable V pl'ios1`:-hatides andedible water soluble hydroxy aci .n

Other objects and t advantages of the invention l will appear from the following description-of preferred embodiments thereof.'4

Thepreparation and properties" of the pre-y cury, while stirring, at a temperature of `150 toV 200? F. When substantially all of the water has been removed from the mixture, the resulting product is soluble in ether and in vegetable and mineral oils and'disperses in water. yIty isa light colored resin, bland intasteneutral (pH` about 6.5), odorless and stable against rancidity'or oxidation. If `relatively pure Imaterials'are employed e" no lfurther purincationis necessary, although, if

desired, the composition may be purifiedby exv tractiony with petroleum'ether or other solvent for the'composition', and evaporating the solvent fromthe extract. Preferablyy a carrier,"usually a vegetable oil such as corn,l cottonses'ame, etc., is incorporated 'vinto thel sodiumI` lactate phatide compositionfin' ythe ilnalstages of dry'- l'solvent is em-v ployed'w Purifyih Obmpcsitirii" In preparing the above'v composition.; the temvratur may vey within; aviderenee.,l for ex'-, e ample fromi'l tov 250, F. Also, *dehydration need notbe carried out' under vacuum, so that the vac-fk uuifmav vary from zero: t0 the vhilillflefstf vacuum commercially' attainable;

` 'required tofdehyd'rate the producti Theygnc'ipor-U- t Ybe' the' @Dumm .propere ti'OSf given' appear In general, sufiicieritl water v l Hslurries maybe unts of waterrequire more used; while 1 large 'am extensive dehydration'treatxnently Furthermore, "contain excess o ff phosphatide or excessv of salt while still retaining the .desirable properties of the composition to a large `the percent of salt added may' the composition degree.' Thus,

'vary between 1 and '15% vofthe weight ofthe produceproducts of the f lactate will rs't'be gr. of corn phosf ut the amount of 'watermay vary widely.' l y t should'be erminloxvredr'y to dissolve the salt,malthough phosphatide.' Furthermore. it is not essential' that a previously prepared salt be employed. Thus, in the above example, sufficient lactic acid and sodium ghydroxideor'carbonat canl'beadded i,.-

to form the sodium' lactate.`A If-it is desied to vary the pH of the resulting'product, excess alkali or e'xcess lactic acid can be employed. The

neutral or acidic compositions are more stable than alkaline compositions. For edible products, therefore, the pH of the composition should not ordinarily be substantially greater than '7 and isv preferably between 5 and 6.8.

Other edible water soluble hydroxy acids can be employed to furnish the acid radical of the salt. Examples of such acids are glycollic, tartaric, malic, citric and gluconic acids. In general, any aliphatic hydroxy acid having a rela.

tively low number of carbon atoms can b e employed in combination with alkali to produce compositions having properties similar. to the sodium lactate composition above described. Aliphatic hydroxy acids containing lcarbon atoms substantially in excess of 7 tend to become insoluble in water, and compositions containing radicals of such acids tend to Ilose their water dispersibility, However, hydroxy acid radicals having more than 7 carbon atoms will form compositions usable for many purposes, and such acids need not necessarily be aliphatic. Examples of other acids forming compositions in accordance with the present invention are salicylic acid, gallic acid, hydroxy butyric, hydroxy glutaric, etc. 'I'he compositions resulting from treating phosphatides with salts of such acids form powerful emulsiiiers and many of them have certain specific properties providing utility for special purposes. For example, an alkali metal or ammonium salt of salicylic acid with phosphatides forms a water soluble composition useful as an analgesic.

Other alkali metals may replace sodium in the compositions above discussed, for example, potassium. Ammonia may also be employed,` and, in general, the ammonium and alkali metal salts of hydroxy acids having a relatively small number of carbon atoms form compositions with phosphatides which disperse readily in water and are soluble in ether and in oils. Alkaline earth metals such as calcium also may form the alkali radical vof the salt and produce, in combination with phosphatides, excellent emulsiflers for certain purposes, but in general such compositions do not have the desirable properties of the alkali metal 'and ammonium compositions. A

For incorporation into food products, "corn phosphatidic compositions are preferred, as they are light in color and free from linolenic acid, thus forming light colored substantially tasteless and odorless phosphatidic compositions which are stable against rancidity, oxidation, reversion', etc. Other linolenic free phosphatides may be employed, such as cottonseed, rape or peanut phosphatides if more darkly colored compositions, orA

in some instances compositions having a characteristic taste, are not objectionable. Even phos-i phatides containing linolenic acid radicals such as soya bean phosphatides and certain animal phosphatides, for example egg yolk phosphatides, may likewise be ,employed to form the compositions of the present invention, although in general such compositions are darker in color andv y not as stable as compositions formed from vegetable phosphatides which are free of linolenic acid radicals. However, the neutral and acidic compositions of the presentinvention, with soya bean and the other 1es's"'stab1e pliosphatides'tre-I ferred to, are much more stable than the original phosphatides. `It is apparent Athat mixtures of different hydroxya'cid radic'als'inaybe employed in combination with mixtures of yva'llrious'alkali radicals vand that mixtures of various phosphatides may also be employed to produce compositions in accordance withl the present invention.

.The sodium lactate phosphatide composition of the preferred. example is an edible emulsiiier and acts as a hydroscopic agent. It forms a gelatinous dispersion in 5% concentration in wav ter.` There is no separation or extrusion of free water. In concentrations less than about 5%, the `solution is homogeneous and no sediment or settling out of the composition occurs, even after prolongedstanding. The composition is a light colored paste, and is not tacky. Very stable emulsions of oil and water are made by employing the composition as an emulsier. As little as 0.1% is effective, and the normal range is 1/2 to 2%. In making such emulsions, the composition smooth stable emulsions of vegetable, mineral and essential oils with water are obtainedwhen 0.1 to 5% of this composition is added to either the water or oil phase, and the resulting mixture agitated. c

- Because of its neutral character, the composition can be blended with ingredients ci' soaps, salves, ointments, face creams, suppositories, shaving creams either ordinary orA brushless, insecticidal emulsions, nose drops, nose sprays, ephedrine nasal preparations, pine cil emulsions or flotation compounds, etc. vThe composition also finds` utility as a pigment dispersing agent for oil paints and as an emulsifler for casein paints in'which the composition also acts as a softener of the film. When incorporated into gelatin, the latter is soft and pliable. As an ingredient in gelatin, cornstarch, chocolate desserts, etc., it performs the functions of increasing ing linolenic or equivalent acid radicals such as.

fish or fish liver oils. It also improves the keeping qualities of the more saturated oils or fats vsuch a's corn or cottonseed oils, margarines, or shortenings. It forms stable emulsions of orthodichlorobenzene in water, which emulsions are used as insecticides and weed killers. When added to mixtures4 of sulfonated oil and orthodichlorobenzene, the composition enhances the emulsifiability of th'ese mixtures. The composition is soluble in orthodichloroben'zene and may be added to thisrmaterial for use alone or'iwith sulfonated oil. It is also useful as a surface tension reducing agent for textiletreatment. Because of its ability to retain moisture, the composition is also suitable for use in tobacco to prevent drying and loss of flavor thereof.

The preferred compositions of the present invention are perhaps of greatest; utility in margarine. 'I'he composition increases the amount of water which is retained by the margarine, and this additional water over that which is retained when the composition is not present is held very ilrmly even at 212 F. The amount of this composition added will range from 0.1 to 5% based \on the weight of the oil or fat in the margarine and the normal amount is approximately .3 to .4%. Because it is bland and light in color, it does not affect the odor, color and flavor of the margarine. The preferred manner of incorporating the composition into margarine is to first mix it with the oil or fat. The resulting mixture is suitable for use in the manufacture -of margarine by the known methods, among which are the chiil vat, chill roll and continuous methods.

The margarine manufactured with this composition has superior characteristics, among which are: (l) smoother and better emulsions in the churn; (2) smoother product; (3) greater adaptability for incorporation of color; (4) marked decrease in sweating, permitting the packing of margarine in weights more closely approximating the actual standard weights, thereby reducing the overweight now necessary; (5) drier packages which are neater because of the elimination of normal sweating, which results in salt stains on the package;v (6) greater spreadability, particularlyin coconut oil margarines; ('Z) increase in temperature range Within which the margarine is plastic, i. e. retaining plasticity at both lower and higher temperatures; (8) retention of larger 'amounts of milk solids and salt, making waste in' manufacture from this source negligible; (9) more butter-like appearance and consistency; (l) greater adaptability for frying because spattering is reduced and eggs or other material are prevented from adhering or sticking to the cooking surfaces; (11) permits the use of margarine containing the composition of the present invention as a high ratio shortening.

'Ihe high ratio effect above mentioned with respect to margarine may also be obtained in substantially dry fats such as the -usual shortenings by the addition of the preferred composition of the present invention in amounts between 0.25 and The usual range, however, for providing optimum high ratio characteristics will usually range between 1.5 and 2.5% in-both margarine and shortenings on the basis of the oil o'r fat present. Such shortenings, or the margarine when used as a shortening, produce cakes of improved texture and volume in the presence of sugar-to-our ratios greater than 1.

details thereof may be varied within the scope of the following claims.

I claim:

1. As a product of manufacture, a composition of matter comprising a compound formed by reacting a phosphatide and a solution of an aliphatic hydroxy acid.

2. As a product of manufacture, the composition of matter resulting from reacting vegetable phosphatides with salts of aliphatic hydroxy acids.

3. As a product of manufacture, suitable for incorporation into edible products as an emulsifier and anti-oxidant, a composition of matter comprising a compound of vegetable phosphatides with salts of water soluble edible aliphatic'hydroxy acids.` 'u

4. As a product of manufacture, a composition of matter suitable for incorporation into edible products as an anti-oxidant, which comprises, a compound formed by reacting a vegetable phosphatide free of linolenic acid and a salt of a hydroxy acid selected from the group'consisting of between a vegetable phosphatide and an alkali` metal saltlof an edible water soluble aliphatic hydroxyvacid.

7. As a product of manufacture, a phosphatidic compound resulting from the reaction between a vegetable phosphatide free of fatty acid radicals of greater unsaturation than linoleic acid and an alkali metal salt of an edible tweena vegetable phosphatide and sodium iac- The sodium lactate-corn phosphatide compoy position is preferred for employment in margarine and shortening because of its light color, stability, neutral reactions, etc. However, it is to be understood that compositions of other vegetable phosphatides, even including the soya phosphatide, may be employed in a similar manner and in substantially similar proportions either in combination with sodium lactate or other alkali metal or ammonium salts of water soluble edible hydroxy acids. These compositions may be also employed for other purposes mentioned in the present application and for certain of such other purposes the compositions including alkali earth metal salts of hydroxy acids in general are suitable.

While, for the want of al better term, I have herein referred to my new chemical compounds as phosphatidic compounds, it is nevertheless to be understood that the same are fundamentally dissimilar in composition, behavior and utility to the usual soy bean lecithin of commerce.

This application is a` continuation in part of my copending application Serial No. 290,083, tlled August 14, 1939.

While I have disclosed the preferred embodiments of my invention, it is understood that the tate.

9. As a product of manufacture, a phosphatidic compound resulting from the reaction between a vegetable phosphatide and sodium citrate.

10. As a product of manufacture, a phosphatidic compoundl resulting from the reaction between a vegetable phosphatide and sodium tartrate.

11. The process of producing phosphatidic compounds with salts of hydroxy acids which comprises reacting a mixture of a phosphatide with a salt of an aliphatic hydroxy acid in the presence of water, and dehydrating the resulting product.

l2. 'I'he process of producingy phosphatidic compounds with salts of aliphatic hydx'olw acids which comprises heating a mixture of an alkali metal salt of an edible water soluble aliphatic hydroxy acid and a phosphatide'in the presence of water so as to react said sait with said phosphatide.' and dehydrating the reaction products. 13. The process of producing phosphatidic compounds with salts of aliphatic hydroxy acids which comprises reacting a mixture of a phosphatide with a salt of. an aliphatic hydroxy acid in the presence of water, dehydrating the resultg product, extracting said compound from said reaction mass with a solvent therefor, and evaporating said solvent from said compound.

BENJAMIN H. THURMAN. 

